What to do — when you don’t know what to do

By Colleen Newvine

Lesley Ware moved to New York City for her dream job. As the new project manager at a national nonprofit serving girls, she envisioned working with a team of smart, liberal women to improve the world. What she experienced was slow-moving bureaucracy.

“Everything about our mission told girls to follow their dreams and learn and grow,” Ware says, “but that’s not how it felt for me in that job.” After five years of yearning to explore, innovate, and develop her skills, she knew she had to find a better fit. The trouble was, she didn’t know where to begin.

Reluctant to give up her steady paycheck without a plan, Ware decided to take baby steps while keeping her day job. It wasn’t a straight line to success, but her steady boldness paid off. Today, she is the author of two books and runs her own business. Here are the three big lessons from her journey.

1. Put yourself out in the world

How she was stuck: Ware wanted to be more creative, but she didn’t know what that meant.

What she did: After her boss said no to a storytelling blog to reach girls, she started a personal one called The Creative Cookie. “My first post was August 28, 2008, and I just wrote, ‘I want to live a more creative life, what does that mean?’ I felt like blogging would hold me accountable for being more creative. I wrote about creative ideas that inspired me, including going to my first Fashion Week.”

What she learned: Get out of your own head. Involve other people. Show your work. By using her blog as a public place to explore her interests, she had an excuse to go to New York Fashion Week and interview inspiring people. She also had a forum where she could get feedback on her thoughts. That helped her realize how drawn she was to fashion. “A friend of mine was introducing me to someone and said, ‘Oh, Lesley has a fashion blog,’ and I said, ‘Is that what it is?’”

2. Prepare for change — even if you don’t know what it is

How she was stuck: The uncertainty of what to do next kept her in a disappointing job.

What she did: When her Creative Cookie blog turned 2, Ware hosted a birthday party for it. That prompted her husband, Kamau Ware, to say, “You’re going to need to make a decision” about your job.

Again, baby steps helped. Every day, she would bring home one thing from her desk. Even though she still didn’t have a clear idea what was next, she says she “wanted to let the universe know I was ready for a change.”

What she learned: Preparing herself emotionally for change made change easier. After a month of Ware slowly clearing her desk, her boss told her that her position was being eliminated. “I called Kamau and I was so excited,” she recalled.

3. Be willing to experiment

How she was stuck: Now free of her disappointing job, Ware continued to wonder: What next?

What she did: Inspired by her husband, Ware gave herself one year to see if she could make a career in fashion. Kamau is a photographer and a keeper of black history who tells stories on walking tours, in graphic novels, and through multimedia productions. In other words, he’s never had a normal desk job. He told his wife, “If I can do it, you can do it.”

Willing to try anything, Ware responded to an ad looking for someone to teach a young girl to sew. Her degree in elementary education helped her get the job. Soon, the girl’s parents referred her to other parents, and Ware’s teacher mindset told her she needed a reference book for her students.

“I went to bookstores figuring I would find several books and couldn’t find anything,” Ware said. “I thought, I guess I’m going to have to write it. That’s how I started writing my first book, Sew Fab.”

What she learned: When you try something new, you don’t have to know what’s going to pay off or what the endgame looks like.

Change doesn’t have to be hard
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